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AI Product Engineer

April 30, 2026

SummaryAs part of Guidewire’s Product organization, you’ll join a team focused on embedding AI and GenAI across our cloud platform to transform how P&C insurers operate and innovate. We work at the intersection of insurance, data, and engineering to deliver secure, scalable products that customers can trust in highly regulated environments. You’ll collaborate across Product, PDO, Professional Services, and Go-To-Market to ship AI-powered capabilities that drive measurable customer value worldwide. The Vision At Guidewire, we aren't just adding a "chat" bubble to our software. We are reimagining the $2 trillion P&C insurance industry as AI-native. This means moving from static forms to dynamic, agentic workflows that can read a 100-page policy, analyze a legal demand, or predict a claim's trajectory in seconds. We need an AI Product Engineer who treats LLMs as a raw material for building magic. You are an engineer with "Product Taste"—someone who cares as much about the user's "aha!" moment as they do about the latency of a vector search. Why This Role is Unique In most big companies, engineers are siloed. In this role, you are embedded with the Product team. You are a co-author of the roadmap. You have the massive data and customer reach of Guidewire, but the autonomy and "move fast" culture of an AI-native startup. "We are looking for the engineer who gets annoyed when an AI response is technically correct but contextually useless—and then stays up late to fix the prompt architecture because they care about the product experience."Job Description<h3>The "AI Intuition" Factor</h3><ul><li>We care less about your years of experience and more about your intuition for the non-deterministic. You understand that:</li><li>Context is King: The difference between a "hallucination" and a "breakthrough" is often just how you architect the context.</li><li>The UX of AI is Different: Traditional UI is about constraints; AI UI is about guidance. You know how to build interfaces that build trust.</li><li>Prototyping is Research: You’d rather get out a vibe-checked prototype in two days to get user feedback than spend two months over-engineering a pipeline that nobody wants.</li></ul><h3>What You’ll Do</h3><ul><li>Design Agentic Workflows: Partner with PMs to decompose complex insurance tasks (like subrogation or underwriting) into multi-agent systems using agent frameworks.</li><li>Rapid Prototyping: Build the "Version 0" of AI features. You will be the first person to turn a PM’s "What if..." into a working demo that feels like the future.</li><li>Own the "Eval" Loop: You won't just write code; you’ll define what "good" looks like. You’ll build the evaluation frameworks to measure accuracy, tone, and reliability across thousands of insurance scenarios.</li><li>RAG/graph Architecture: Implement sophisticated Retrieval-Augmented Generation and graphs that can navigate the labyrinth of Guidewire’s multi-tenant data structures.</li><li>Bridge the Gap: Act as the technical translator between the "Art of the Possible" (Frontier AI) and the "Reality of the Regulated" (P&C Insurance).</li></ul><h3>Your Toolkit</h3><ul><li>The AI Stack: Deep experience with OpenAI/Anthropic APIs, vector databases, and orchestration layers.</li><li>The Core Stack: You are a polyglot who can move between Python (for the AI/ML heavy lifting) and TypeScript/Java (to integrate with the Guidewire platform).</li><li>The Product Mindset: You’ve likely built your own side projects or worked at an early-stage AI startup. You understand user friction and how to solve it with LLMs.</li><li>Problem Solving: You don’t wait for a spec. You see a manual, "boring" insurance process and immediately start mapping out the agents needed to automate it.</li><li>Experience with Voice agents a plus</li></ul> The US base salary range for this full-time position is - . Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.Disability Accommodations and Guidewire’s Appeals Process. Guidewire provides accommodations to the hiring process to create a fair opportunity for candidates with disabilities to contend for open positions. Accommodation requests should be directed to Accommodations@guidewire.com. If things do not go as hoped, we invite you to use our appeals process. Guidewire promises to independently review any denied accommodation and any decision not to offer you the position. The appeals process is the same in either case. Within five business days of receiving a notice of denial of an accommodation, or receiving a notice of your non-selection for a vacancy, e-mail Accommodations@guidewire.com to make an appeal. Guidewire will assign a new decision-maker to review the request and/or hiring decision, who will then notify you in writing of a decision within 10 business days.About GuidewireGuidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540+ insurers in 40 countries, from new ventures to the largest and most complex in the world, run on Guidewire.As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC. Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...